AI Will Revolutionise How You Travel, Priceline CEO Says

With its 1997 launch as a name-your-own-price site, Priceline helped usher in the era of online travel booking―and the growth of a trillion-dollar category. Priceline itself has mushroomed into a global business with 1,500 full-time employees; along with global airline bookings, the site claims to offer 1.2 million accommodations in 116 countries.

Now, the Connecticut-based company is focusing on generative AI, and CEO Brett Keller is behind the leap. It’s just the latest technology push from Keller, a 25-year veteran of the company who has also served as CMO and COO. Under Keller, Priceline launched the travel industry’s first full-service mobile app in 2009; he also helped conceive the hugely popular William Shatner-fronted “Negotiator” ad campaign.

Keller, 56, talked to Penta about how AI is changing travel planning, what luxury travellers do to save money, and why Japan blows his mind.

Penta: Much of Priceline’s marketing is about value. Do you see luxury travellers in your customer mix along with budget-conscious travellers?

Brett Keller: High-net-worth consumers take a significantly higher number of trips than the average leisure traveller. For a high-end vacation like a safari in Tanzania, they’ll work with experts. But for the other 30 trips they book that year, either for themselves or family members, they don’t always reach for the stars. They want to manage money effectively. And as they’re moving around the country and the world, they need a fast, easy way to book travel that accommodates their needs. Priceline is a great platform for that kind of trip. And if you’re taking a quick weekend trip to Miami, and want to stay in the Four Seasons, we’ve negotiated with them. Even high-net-worth individuals seek value.

Priceline made headlines last year for partnering with both Google and OpenAI on Penny, your AI assistant. How has Penny evolved?

She’s gone from, “I can answer questions about the hotel you’re looking at” to actually servicing the customer through more complicated scenarios. If you need to cancel a hotel that’s fully refundable, you can do it with one click. But if there are issues, like a reservation that’s not fully cancelable, Penny can walk through those steps for you.

Penny’s also helping people find, search, and book properties. For example, if the customer tells her, “I’m looking for a great resort with these features, anywhere warm”—she’ll present recommended properties that meet those requirements. You can continue with Penny on the site, or go with the traditional experience.

Has there been any pushback from consumers about Penny and generative AI?

There has been none. Customers still have access to phone agents. Anyway, the younger generation doesn’t want to talk to anyone. And with traditional chat agents, live agents, or even messaging apps, there’s typically a delay. Penny answers immediately and in real time.

What’s the future of generative AI and online travel booking?

The future is a highly personalised shopping experience. It’s hard to achieve, because we don’t know about the consumer when they come in. But generative AI lets us dramatically improve personalisation. As you work with Penny, and tell us your preferences, the way you interact lets us find and book the best products and services every time you return. The ability to customise and personalise increases exponentially.

Is the travel experience even more bifurcated between elite, ultra-high-net-worth travellers and everyone else?

Consumers seem to be a little less sensitive in some areas. On planes, first-class and comfort-plus seats are the first to go, most of the time, and people are burning through points to sit in the front because they’re tired of not having legroom. But seats are packed in economy, too, so people are flying.

Hotel bookings are more economically driven in the U.S. Higher-income people are not as affected by interest rates or the cost of living, so they spend more freely than economy-minded consumers. There is a bit of bifurcation there. The low end is not filling, but the high end is.

It’s been reported Europe’s going to get even more crowded this summer. Does Priceline ever suggest alternatives to over-touristed or overpriced destinations?

We’re not in the business of telling you where you shouldn’t travel. We market popular destinations because that’s where people want to go. As much as we could tell people, “Las Vegas is overcrowded, don’t go,” people will want to go.

Social media is highlighting some overpopulated destinations and suggesting alternatives, so that comes back to us. But price is the No. 1 motivator. Vegas is a great value. There are so many hotel rooms available that you can go in a non-peak period and get a room in a four-star hotel for US$120. Try doing that in New York City.

What destinations are going to pop over the next year or two?

Asia will continue to be exciting and interesting to people. Bangkok is a great place to move in, then travel throughout Southeast Asia. As the region gets more popular, people will keep trying to find more remote and more unique destinations. People love Europe, but it was the hot spot in 2022 and ’23. Some travellers are saying, “I’ve had enough, and I’m moving on.” Japan is also amazing, for so many reasons. It’s easy to navigate. English is not a challenge. It’s safe. It feels like a different world, but completely first-world. The strength of the dollar is also driving some of that―again, price plays a role.

Beyond that, Mexico and the Caribbean took a real hit in 2022 and ’23 after a boom in 2021. They’re coming back now. A lot of people don’t want to travel far—“I just want to go to a beach and not think of anything.” And because not everyone wants to travel overseas, unique and relaxing cities like Nashville, Tennessee; Houston; and Austin, Texas, will be popular, especially into the fall.

Every day brings more headlines about airline woes. Who gets blamed if a Priceline customer has a bad flying experience, you or the airline?

When you have a bad experience traveling, you want to blame everybody. No matter what happened, the online travel agency takes blame and the airline takes the blame. It could be your seat, the person sitting next to you, whatever. We get the complaint, and we take on that responsibility and that role. We have leverage because of the amount of business we drive to partners. They want to work with us to make sure the customer has the best experience. Something goes wrong almost every time you take a trip. That’s just the reality.

What are your favourite places to travel?

My favourite destination, and a place where I spend a lot of time every summer, is [resort town] McCall, Idaho, one of the most beautiful towns in the West, with hiking, trails, and mountain biking. Outside of the country, it’s Japan, absolutely. Tokyo is the most exciting city in the world. It’s mind-blowing.

This interview has been edited for length and clarity.

What’s more important than being a good employee right now? Looking like a good employee in the eyes of AI productivity trackers that more managers are using to evaluate their teams.

Employee-monitoring systems are especially popular at tech companies and are also used by other white-collar firms that want to probe how people spend company time. The scary thing: You might not even know you’re being watched because many states don’t require disclosure.

Metrics can include performance data that is undoubtedly relevant, such as sales results. But it also can employ dubious proxies like keyboard strokes and how often your computer screen goes into sleep mode.

We generally accepted, or at least understood, heightened surveillance during the work-from-home era. Back then it seemed reasonable for bosses to keep tabs on employees they couldn’t see.

Yet the oversight has only escalated, and tensions are rising, too.

A group of former Meta Platforms employees alleges in a lawsuit that the company used a “constellation of internal artificial-intelligence systems” when it began laying off about 10% of its workforce in May. Meta says humans make termination calls.

However that case shakes out, a couple of things are clear. Companies eager to gauge which employees are locked in now have sophisticated AI monitoring systems at their disposal. And they believe they have leverage in a tepid labor market.

So while we may chafe at having our worth reduced to numbers on the boss’s productivity dashboard, we have to play the game as it’s being played. Here are some tips, based on conversations with people who make employee monitoring systems—and others who game the systems.

Be meticulous about your calendar

Calendar integration is one way that productivity trackers have gotten more advanced and, ostensibly, fairer.

Let’s say you make an old-fashioned phone call or attend an in-person meeting. Your Outlook or Slack status may switch to “away,” making you appear as inactive as if you were taking an extended coffee break.

Employee monitors like one made by a company called Insightful cross-check your online status with your calendar to see whether there is a valid reason for your apparent inactivity. If that call or meeting is on your schedule, then the system will recognize that you are busy offline. If nothing is on the books, it could look like you’re slacking off.

Hit the activity sweet spot, around 80%

Let’s not go any further without addressing the underlying question: How much downtime is permissible during the workday? After all, people have been scared to let managers see anything non-work-related on their screens since personal computers first arrived in offices.

No one knows this better than Roger Wagner, who is widely credited with creating the first “boss button” in the early 1980s. He designed a keyboard shortcut to instantly display a spreadsheet if the boss walked by your cubicle while you were playing a computer game. Boss buttons have been features of countless diversions since. (I confess to using one built into a March Madness streaming app.)

Wagner, the founder of computer-education company 1010 Technologies, says his original design was a joke—more of a commentary on overbearing managers than a cover for lazy employees. Good bosses understand workers need mental breaks throughout the day, he says.

This matches what I heard from Insightful Chief Executive Ivan Petrovic. He says customers that use his company’s workforce-management platform don’t expect employees to stay on task 100% of the time.

“On average companies are aiming for 60% to 80% of your time being utilized for work during the day,” he says.

Go ahead and exhale. It’s probably OK to watch an occasional YouTube video at your desk.

And if you’re going to artificially inflate your activity level, be careful. Hitting 90% could look suspicious.

Get physical

So don’t leave your mouse jiggler on all day. Choose the right one if you must resort to shenanigans.

There are lots of software applications that mimic the movements of a computer mouse, so you can appear to be working while away from your desk. There are also devices that plug into computer ports and do the same thing.

Corporate cybersecurity systems increasingly block these apps and devices, and productivity trackers claim to be able to detect them. But some workers swear by mouse docks, like one made by Tech8 USA, that keep cursors moving. The company originally made mouse-moving software but now focuses on physical jigglers.

“People are drawn to mechanical solutions because they’re so simple and don’t require software,” says Tech8 Marketing Director Sam Matthews. “As monitoring technology becomes more sophisticated, that distinction has become even more relevant.”

Use AI, but not too much

Another popular metric for employee-monitoring systems is AI usage. Companies want to know who is embracing new tools, and it can be tempting to think more is better.

“There’s a performative aspect where employees overblow their usage of AI so that they appear relevant in the organization,” says Andrea Derler, principal researcher at Visier, which helps companies track and analyze employee work habits.

In a recent Visier survey of 1,000 U.S. workers, 48% admitted to exaggerating their AI usage.

This is already an outdated strategy. Using AI for everything used to score points for experimentation. Now it can seem wasteful because many companies are watching AI token spending more carefully.

Look, productivity theater has always been part of work. Most of us aren’t trying to cheat the system, but expectations are changing so quickly that we need to be savvy about what the latest employee trackers are looking for.

Sometimes it takes a little gamesmanship to get full credit for our contributions.

AI Will Revolutionise How You Travel, Priceline CEO Says

As AI productivity trackers reshape workplace evaluations, employees are learning how to manage calendars, activity levels and AI usage to ensure their contributions are recognized.

Be meticulous about your calendar

Hit the activity sweet spot, around 80%

Get physical

Use AI, but not too much